| Chic Young creation | 19 |
| Chic Young creation to a treehugger | 36 |
| Chic Young strip | 16 |
| Chic Young's dimwit character | 33 |
| Chic's Broadway partner | 27 |
| Chic, '60s-style | 20 |
| Chic, 1960s style | 17 |
| Chic, 1960s-style | 17 |
| Chic, and then some | 19 |
| Chic, for short | 15 |
| Chic, in a 1960s way | 20 |
| Chic, in the '60s | 21 |
| Chic, in the 1960s | 18 |
| Chic, to Austin Powers | 22 |
| Chica or Raton | 14 |
| Chicago | 7 |
| Chicago from St. Louis | 23 |
| Chicago in a song | 18 |
| Chicago 'L,' e.g. | 25 |
| Chicago "Baby, What a Big ___" | 40 |
| Chicago "Hard ___ to Break" | 37 |
| Chicago "What Kind of Man Would ___?" | 47 |
| Chicago "You're ___ Alone" | 40 |
| Chicago 11 | 10 |
| Chicago adjective | 17 |
| Chicago air hub | 15 |
| Chicago airport | 15 |
| Chicago airport code | 20 |
| Chicago airport control center | 30 |
| Chicago airport letters | 23 |
| Chicago alternative to O'Hare | 33 |
| Chicago and Boston | 18 |
| Chicago animal | 14 |
| Chicago architect Burnham | 25 |
| Chicago area | 12 |
| Chicago area, with "the" | 34 |
| Chicago athlete | 15 |
| Chicago attraction | 18 |
| Chicago baggage letters | 23 |
| Chicago balloonists' needs? | 31 |
| Chicago ballpark eponym, once | 29 |
| Chicago ballplayer's interviewer? | 37 |
| Chicago Band The Walk-___ | 25 |
| Chicago band who make one-take viral videos | 43 |
| Chicago band whose one-take 2005 video was choreographed and filmed in their backyard | 85 |
| Chicago baseballer | 18 |
| Chicago basketball team sold to the Vatican? | 44 |
| Chicago bearers? | 16 |
| Chicago Bears coaching legend George | 36 |
| Chicago Bears coaching legend Mike | 34 |
| Chicago Bears founder George | 28 |
| Chicago Bears head coach Smith | 30 |
| Chicago Bears star Devin | 24 |
| Chicago Bears' coach | 24 |
| Chicago Bears' field | 24 |
| Chicago Bears, e.g. | 19 |
| Chicago Blackhawks goalie Khabibulin | 36 |
| Chicago Blue Line terminus | 26 |
| Chicago business area | 21 |
| Chicago business district | 25 |
| Chicago cable station | 21 |
| Chicago cagers | 14 |
| Chicago campus | 14 |
| Chicago cap letters | 19 |
| Chicago carriers | 16 |
| Chicago city council mem. | 25 |
| Chicago Classic restaurant chain | 32 |
| Chicago clock setting | 21 |
| Chicago clock setting: Abbr. | 28 |
| Chicago club | 12 |
| Chicago columnist Kupcinet | 26 |
| Chicago community | 17 |
| Chicago commuter carriers | 25 |
| Chicago commuter options | 24 |
| Chicago company | 15 |
| Chicago conveyance | 18 |
| Chicago cop Lieberman in Stuart M. Kaminsky novels | 50 |
| Chicago Cubs e.g. | 18 |
| Chicago Cubs spring training site | 33 |
| Chicago Cubs' field | 23 |
| Chicago Cubs' station | 25 |
| Chicago daily, briefly, with "the" | 44 |
| Chicago daily, familiarly | 25 |
| Chicago daily, for short | 24 |
| Chicago daily, with "the" | 35 |
| Chicago deep dish chain | 23 |
| Chicago description | 19 |
| Chicago destination | 19 |
| Chicago diamond cutter? | 23 |
| Chicago dinosaur | 16 |
| Chicago district | 16 |
| Chicago district (with ''the'') | 47 |
| Chicago district, with "the" | 38 |
| Chicago Eight defendant | 23 |
| Chicago Eight defendant Bobby | 29 |
| Chicago el feature | 18 |
| Chicago eleven | 14 |
| Chicago embrace? | 16 |
| Chicago entertainment district | 30 |
| Chicago event | 13 |